Show transcript:

Welcome to The Broad Experience, the show about women, the workplace, and success. I’m Ashley Milne-Tyte.

This time, leaving a job for a new work life – even if you don’t yet know what that life will look like…

“There becomes this thing inside of us that we know if we don't jump we're going to die inside just a little. And so that impulse just becomes so strong we have to listen to it and the emotional simply outweighs the functional.”

But you may have to work out who you are when you’re no longer your job…

“I started to question whether I had ambition anymore. Like did I lose it somewhere or did I drop it and did it roll it into the sewer. Because I had always had it. I'd always had a huge ambition.”

Coming up – disrupting yourself, what can happen afterwards, and re-defining success.

But first…

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The end of one year, the beginning of a new one – it’s a time when a lot of us think about where we are in our lives and what we might like to change. In this show we’re going to talk to two women who changed their work lives dramatically. They essentially jumped into the unknown. One was restless at her job, the other was much more unhappy. But each of them felt it was time to go.

We had a 3-way Skype call. I asked each woman to introduce herself.

“Hi, this is Tess. I am a former public radio host and current author of the book Leap: Leaving a Job with No Plan B to Find the Career and Life You Really Want.”

“Hi, this is Whitney Johnson. I’m a former Wall Street Equity analyst. I co-founded an investment firm with Clayton Christensen at the Harvard Business School, and I am the author of Disrupt Yourself: Putting the Power of Disruptive Innovation to Work.”

I know Tess Vigeland from Marketplace, the public radio business show here in the US. I used to listen to her all the time, then I began working for Marketplace myself. Tess hosted the morning show for several years, then she hosted the weekly personal finance show Marketplace Money. And then, at the top of her game…she left. We’ll talk more about that in a bit.

Whitney Johnson started working in finance as a secretary – she had a music degree and zero business experience. But over the years she was promoted again and again and she became a successful research analyst, analyzing different companies’ stock. And then she too quit. She left that unexpected career and that big paycheck… to become an entrepreneur.

Disruption is probably a familiar term if you’re in the start-up world or even the wider business world. Whitney calls this type of move personal disruption – you start at the low end, climb to the top as she did, then you jack it all in to start all over again, and learn a whole new set of skills…

“Initially I felt this absolute thrill, this exhilaration, like you know I've just jumped off of this huge peak. But then there were moments where I felt this loss of identity. I could no longer call people and say it’s Whitney Johnson from Merrill Lynch, it was just now Whitney Johnson, and there have been certainly lots of days where the P. E. or puke-to-excitement ratio has been so incredibly high I feel like I'm on this thrill ride to zero cash flow. So it's been scary, it’s been lonely, but one of the things I've discovered about disruption is that if it's scary and lonely I'm usually on the right track.”

AM-T: “Tess…weigh in.”

“The thrill ride to zero cash flow, I’m familiar with that. So yes, I actually disrupted myself before even knowing what that phrase was, what it meant. And I'm grateful to Whitney for identifying it because it's a really scary thing to do when you think that you're all alone and you're crazy. And that's pretty much how I felt when I left my career, my twenty-two year career in public radio. It was what I worked for my whole life. From the moment I left college. And I got it at age thirty-two. And for eleven years I was with a program that you and I know very well, Ashley, Marketplace. We both worked there. And I had an anchor job. And all I ever wanted to do was be famous on the radio and all the sudden that's what I got.

And I spent eleven years there including six years in personal finance. And then, for all kinds of reasons, I left. And usually when you leave your dream job is for the next dream job, it’s for the next great thing that you're going to do. And I didn't have that lined up. And I left without having any idea what I wanted to do next - we're all supposed to have that dream that we're going to do next that the thing that we want to follow, that passion we want to pursue and. I didn't have that because I actually really loved my job. So for me the disruption was total, it was extraordinary. And it was awful. For the good part of the first part, and you know slowly over the last three years now I've learned that it was absolutely what I was what I was supposed to do. But I certainly didn't know that at the time.”

AM-T: “Whitney, you advocate disruption regardless of whether you’re in a situation you feel you have to get out of. Why should somebody do that if they’re feeling sort of fat and happy?”

WJ: “Oh, well…when you put it that way. What I would say is that if you think about – I think every human there's an imperative to actually move forward from stuck to un- stuck, to become more, become who you could be, not who you are. What I would say and I think this really goes to Tess’s idea and her story, is that…whenever we hire a job, we hire it to do and functional and emotional job for us. And a functional job is to put food on the table and to you know, basically be fat. But there's this emotional job that you're hiring your job to do which is, it can be satisfaction, it can be prestige, it can be stature, it can be learning – whatever. And almost always when we make that jump we're making the jump because the job no longer does the emotional job for us, and I suspect Tess if we were really to peel back the layers of why you made the leap and why I left Wall Street there were emotional jobs that were no longer being done and so there becomes this thing inside of us that we know if we don't jump we're going to die inside just a little. And so that impulse just becomes so strong we have to listen to it and the emotional simply outweighs the functional.”

TV: “Yeah, I would totally agree. And you know I would also argue that I was comfortable. I mean sure, I had things that were going on at work and yes, I was kind of tired of the subject matter and all that, but there was nothing like WRONG wrong. Nobody had kicked me, there wasn't anything that I could point to and say, ‘That is absolutely the reason that I should walk out this door.’ It would have been way easier to just stay there and be comfortable and do a job that a lot of people covet, and just to stay in what I intended to do which was, you know, die at the microphone. So for me it was actually much more, I mean it really was disruptive. Because it wasn't what I was supposed to do. It didn't make any sense, at least at the time.

But for me it's exactly what Whitney is is talking about, there were these emotional pulls that I was dealing with and I don't know why I listened to them at the time, people have asked me, why did you finally just decide to go? And it’s very hard to explain. But there was just a point at which I was like, you know, I'm not getting from this job what I need to get. You’re right, I hired it for a reason. And it's not performing for me. And I had to be selfish and say you know what, I need to do what’s best for me. And that means leaving without having any idea what comes next.”

AM-T: “It's interesting this idea of hiring a job. I bet most people do not think about it like that.”

“No they don't. That's one part of Whitney's book that was really eye opening for me. You know I never thought of it that way and I think it's a much healthier way to think about it. I think that shows a confidence in yourself when you're saying that you're going to hire the job. I mean, and that's the way it should be right? We are talent. We are the product. So I wish a lot more people would take what Whitney says and really absorb that and think about it that way.”

Still, making this kind of leap isn’t easy. Tess describes the aftermath as a rollercoaster. You leave, and then you think what have I done? All your security has gone. Yes, you left the politics and perhaps the toxicity of your workplace behind…but now, you’re on your own.

TV: “You know I would go through those valleys where I felt I was just a complete dolt for leaving my job and then I would have these peaks where I would have an independent project, I was working on some freelance project. And I would finish it and I would feel like wow - I did this on my own! I'm working for myself. And it is actually coming to fruition and I'm making money and I'm feeling good about the job I'm doing. But then of course the next day I wouldn't have that project any more and to be like, oh my God, I'm never going to work again. So it is it is very much a roller coaster but I tell you what I've learned is that those swings on the rollercoaster are a hell of a lot more interesting and exciting than the merry go round. “

WJ: “Yeah, and what I would say, I would add is, I think about the work that I do now and it absolutely is a roller coaster and there are absolutely days that I feel scared and lonely but I also know that the work that I do now, I would say ninety percent of the time is exactly what I want to be doing. And Tess, you kind of alluded to this, this notion of when you work for yourself you have to actually figure out what your value is in the marketplace, and you have your strengths and you have to learn how to negotiate. So there's all these things that when you're inside of a large corporation, you can like sort of not own any of your power, because you negotiate your salary once and then after that you go about your business and you may negotiate three or five years later. Now we're continually every single day figuring out what our value in the marketplace is. And there's this whole notion of eating what you kill. And I and I hate to say it but I'm an adrenaline junkie, and every time I get a check in the mail my daughter, who’s 15 years old, laughs at me because I’m like, I love money. And she’s just like, really? And I’m like, yeah… you get that dopamine squirt when you get a check in the mail that you just simply don't get when you're working for someone besides yourself.”

AM-T:“But I’m going to step in and be that voice of reality of whatever you want to call it… Because you’ve both come from high paying jobs and industries, I mean Whitney, Wall Street, it goes without saying…and Tess, you were a national host…now as somebody whose most recent check in the mail was three hundred dollars, I can tell you now of course I was glad to get that three hundred dollars. But it wasn't six thousand dollars or fifteen thousand dollars. And for those of us who aren't in quite such a sort of high position…you two were able to do this because you did have a cushion. And what about people who don’t?”

TW: “You know this is a question that I've gotten more than more than any other as I’ve talked about the book and its process and. You know I would say, I’d outright acknowledge that there is a privilege to be able to quit your job without having anything else lined up. Now that said, I do think that people can work toward being able to do it, it’s very difficult. But you know I think that we tend to look at our lives and say, well, this is what it's supposed to look. I have to have X. and Y. and Z. in my life or it's not going to look right. Well, if you adjust some of those expectations of yourself, which means, ignoring what you think everybody else thinks of you, then you know maybe you can take a second job for a while, maybe you can cut back on expenses somewhere, maybe you can even downsize your home. You know it depends what you're willing to do to make a better life for yourself, a better work life for yourself. But yeah, I absolutely was very fortunate that my husband at the time was able to pay the mortgage. And there's no way that we could have done it if that had not been the case. But again, it really is a matter of setting your priorities. And also being willing to step back, to step down from that lofty salary, from that lofty paycheck. I mean my first year out I made about a little over half of what I had made in salary and it was really hard because you know, I think we identify ourselves a lot with the with the money we bring in, with the title that we have. And I didn't have any of that anymore. And I had to figure out how to make the budget work on a lot less, and I was the primary breadwinner in my family. I made more money than my husband. So it was a long way to come down. And there's a lot of psychological emotional turmoil that comes with that.”

AM-T: Whitney?

WJ: “Yeah. I have so many ideas going through my head. I think first of all I would say, you're right, Ashley. There is a privilege that come with being able to have somewhat of a cushion. Two thoughts there, the first is that sometimes people use that cushion notion as an excuse. I remember someone saying to me well, I can’t quit my job. We did the five whys and it came down to it and he could, he had ten years' worth of savings in the bank, so I think the first thing I would say to someone when they say they can’t is, is that really why you can’t?

And the second thing I would say is there’s one thing to make a lot of money and there's another thing to actually save a lot of money. And that's something that I'm actually really learning how to do it to save and to build wealth in a way that I hadn’t when I was making a lot of money. And so I think that's been a really good important lesson for me, but I would add there, this is something that I touch on in the book is this notion of constraints. When you don't have as much of a cushion available to you, you figure out how to make money a lot faster than you would if you did have a big cushion. And it was only when I found that I was going through my nest egg - because interestingly I'm also the primary breadwinners as well – that I started to tap into what my real strengths were. Up until that time I could sort of dabble and go, I think I'm good at that and I think I'm good at the other thing. It was when, ‘OK, are we going to have money in the bank?’ that I started realizing what am I actually really good at that I do naturally that people would actually probably pay me for that right now I don't charge them for because it's just easy and fun?”

One of the things Whitney and Tess get paid for these days is public speaking. But that brings us to another point Whitney makes in her book about disruption – failure is usually part of the process. In her case, one day in particular sticks out.

WJ: “What happened is I was giving a speech, and sometimes I have performance anxiety. And I was up in front of people, there were a couple people in the room that I really cared about what they thought of me. And so I had a panic attack, or a stress episode is probably is a better way to describe it. And so I started talking, and I even had things written down so it’s not like I forgot what I was going to say, and I just kept getting sweatier and sweatier and sweatier, and you know just sweat dripping down my face so by the time I finished I looked like I’d run three miles. And that was really hard for me because I felt this intense experience of shame.”

She really had to work to divorce herself from that awful feeling…

WJ: “You know our society teaches us that our identity is equal to our successes and we learn that from a very young age. And so what I'm having to learn is OK, if I succeed or fail in any given moment, it has nothing to do with my sense of worth or my ultimate worth.”

TV: “We are always, always are harshest critics.”

AM-T: “And dare I say women are more so our harshest critics…”

“Well yes, and Ashley, so I would add there, so the other day someone asked me like which of these variables is harder or easier for women? I would say that the failure is the harder one for women because we tend to judge girls on their track record. And we tended to our judge boys on their potential. So every time a girl makes a mistake then that means her track record just got worse. And so her prospects for the future got worse so we feel more shame around it than a boy who we’re just like oh, that's OK because you know he'll do it better next time. So I do think that failure is especially acute for women, vis-a-vis men.”

AM-T: “Yeah and also you pointed this out and this is so true, that we’re the ones who pay attention in class, we’re the ones who think it's very important to do well in school and we measure ourselves by that kind of success. But then when you get out into the real world. And you realize that there are politics involved in the workplace, and you are not being judged on that essay you did, it's about so much more than the work you're putting in. I think I think women – a lot of us don't have that political savvy, we think that all you have to do is beaver away and you'll be rewarded, and that just isn't true.”

WJ: “Right, right. Which is why when my daughter says to me she’s going to go negotiate with her teacher I’m like, ‘You go girl.’ Because I know she has to get that skill. She needs that skill.”

May she become a master negotiator.

Now one of the most interesting things for me about Tess’s book Leap was that she really had a hard time in the aftermath of leaving her job, and not just in the first few months. It wasn’t a case of leaving an unhappy situation and finding her true self in the outside world. Far from it.

AM-T: “You’re really wrestling with yourself a lot during the book. There’s a lot of questioning of yourself, of you asking yourself why in the earlier months, years it was so hard for you to be in this new situation. You go in and analyze yourself. And I was as so interested in the part where you talk about ambition and the role ambition has played in your life, and you spoke to your parents. Can you talk about that, and what your dad said?”

TV: “Yes. So one of the biggest things for me when I left my job was that I felt like I was stepping away from something that I was supposed to be doing, that I was voluntarily leaving something that was so great -- and you know just to pick up on some of what Whitney just said, I think that particularly as a woman, you know I basically, what I did was I leaned out. And that is not what we are supposed to be doing these days as we all know. You know what I should have done, I kept telling myself you should've just stayed he should've kept pushing and pushing and pushing for that job that you really wanted, that you knew you were never going to get because there was a glass ceiling. But you should have kept trying, to have kept going, because that's what we're all supposed to do, especially as women – if you reach a certain point in your career, you are not supposed to step back. Much less step off the ladder. But that’s what I did, and I started to question whether I had ambition anymore. Like did I lose it somewhere or did I drop it and did it roll it into the sewer. Because I had always had it. I'd always had a huge ambition. I mean I said right off the bat here that I wanted to be famous on the radio. And I got that and I worked really hard to make that happen. So I wanted to explore why I was so obsessed with this idea that I had failed in my ambition. That I had failed in not really pursuing it to the ends of the earth.

And so I sat down with my parents. This is one of the great advantages of being a journalist and a book author is I actually had an excuse to sit down with my parents and stick a microphone in their faces, and we spent a long time talking about the whole notion of career. What it means, what it means to love your career. And then I asked them, I said, you know I have been feeling so bad about this and trying to figure out why it's so important to me to have a really high profile job. Why was I obsessed with that? Why was I so ambitious that all I wanted to do was be famous? Because there's no fame in my family. This didn't come from anywhere or from how I was raised, I just for some reason had this gene in me, and my dad said something to me that I will never ever forget. He said, ‘you know what Tess, I think when you were a kid you didn't like yourself very much. And I think what you've been doing ever since then is proving to people that you are valuable. That you mean something in this world.’

And of course I started crying and said, you're absolutely right. This is all about how I have felt as a girl, as a woman, as a person on this earth. And how I've never been truly comfortable with myself. And so for me a lot of the last three years have been coming to grips with who I am outside of what I do. Figuring out what my value is if I'm not, you know, some famous news broadcaster. People will still recognize my voice in the elevator and I love that. But I certainly don't have what I used to have. But at the same time I've also learned to let go of the external notions of what it means to be successful.”

AM-T: You talk about this at the end of the book as well, you call it ‘giving the middle finger to the success ladder.’

TV: “Did I say that? Yeah…we all I think especially in this country we grow up with this picture of what it means to be successful. Of what that looks like. And it's money. It's things. It's where we live, it's what we drive. Now we all know that that's not supposed to be important, but it just becomes important. And it becomes the way that you show that you have made a good life for yourself. And I had all that. I had all of it. You know I checked off all the boxes that I was supposed to check off to have that life, the only one I didn't check off was having children. But I checked off everything else including the dream job. And then I walked away from it and I had to figure out then what that new definition was for me. And is still evolving, I still don't know what it is and people are constantly asking me how do you know what your definition of success is, and how can I apply that to my life? My answer to that is, I don't know what your definition is and I would hope that at some point we would all have different definitions. Because we're all individuals, we all have totally different lives that we're living and it shouldn't all be the same. And so why strive for looking the same? Why use some external measure of what that success is supposed to look like?

And as a preview, I am actually right now in the middle of unchecking all those boxes that I checked off, so I already checked off the career box. I’m now checking off the homeownership box, I'm checking off the ‘I have a bunch of things’ box. And I even unchecked my marriage box. And I am literally leaving the country in three weeks to travel and not have any of that comfort around me. Not have any of those notions of success around me at all, it's going to be me and two bags. And that's it. And so I'm kind of forcing myself into an even newer definition of what that success looks like and I don't know what I'm going to be.”

WJ: “You're leaping again.”

“I'm leaping again. Yep, I’m totally disrupting myself again.”

WJ: “That’s exciting.”

“It is. It’s scary. I’m terrified. But I did it three years ago and it worked out pretty well, so why not do it again?”

Tess Vigeland and Whitney Johnson. We had this conversation a few weeks ago. Tess has in fact just flown off to southeast Asia – for what she hopes will be at least a year. She says it’s her first ever year where she doesn’t have a plan.

That’s The Broad Experience for this time. You can post comments on this episode on the website or on the show’s Facebook page.

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